My Girlfriends Younger Brother

By v m

Published on Apr 8, 2002

Transgender

My girlfriend's younger brother part 2 by Freethinker32@yahoo.com

This story involves teenage crossdressing and sex. Only read if you of age and like this type of material. It is purely fictional. I hope you enjoy. Feel free to email me with comments, flames will be ignored. :)

It hasn't been that long since Eric (Brooke) and I were together for our first time. So far Beth and their family are none the wiser to our escapade and we intend to do our best to keep it that way. During this time, Eric and I have continued talking but not all that much more. I will tell you now about the next two times something happened between us.

The first time occurred about two weeks afterwards. It was nothing major but we both enjoyed it. Beth and I were over visiting their parents one bright sunny weekend afternoon, planning to spend the day there and then go out to dinner. As evening drew closer she comes and informs me that her parents have invited to have dinner with them. Not wanting to be rude I said it was cool with me and so she returned to them to tell them the news. There were still a couple hours remaining until we ate so I lounged around, not doing much, while she was helping her mom get things prepared. Her dad was outside cutting the grass so I was left to tend to myself. Nothing new, I am pretty much accepted as part of the family here. Finding nothing on tv, I decided to go see what Eric was up to. Not planning to do anything with all these people here, just see how he is. I told Beth and her mom what I was doing as I walked up the stairs and was just told for us to be down in an hour or so. Agreeing to that I went to his room and knocked.

He answered the door with a small surprise on his face and invited me in. "Hi Brooke" I said as I sat on his bed.

Shyly looking down a bit, he replied "Hi Mark"

He sat at his desk, about 5 feet from me as we had some small talk. The normal, what's up? Anything cool happening? What have you been up to? Stuff like that. I could tell he was a bit nervous.

"What's wrong, why so nervous?"

"Uh...no reason" He said as he looked towards the door.

I let out a small laugh. "Don't worry, I wasn't planning on doing anything if that's what has you bothered."

"Oh, ok. It's not like I don't want to, we should just be more careful. Last time sis could have busted us."

"Yeah she could have but she didn't." Thoughts came back to me about that day and naturally I began to get turned on. I patted the bed next to me, "Come sit by me sweetie."

"I really shouldn't"

"Don't sweat it, mom and sis are fixing dinner and you can hear your dad outside cutting grass. No one will bug us, come sit with me."

He slowly got up and came over, sitting next to me. But before he could I reached up and grabbed him by the waist and pulled him to me. At the way we were, I seated and he standing, his crotch was face level to me and I buried my face in it, kissing his cock through his jeans. He tried to pull away a little but I had him good. I could feel him start to grow.

"I told you last time I would do something for you, and now is that time."

I went back to kissing his dick for a few moments as he nervously kept looking back towards the door.

"Ok, if you're that worried about someone coming in the door, turn around." With that I turned him around so that his butt was now facing me.

"MMMMM how I missed this ass" I said as I began to kiss it. It was so nice in his jeans I wish I could nail it again right now but that wouldn't be all that possible and would take too much time so I decided to do that next time.

"Ok hon, it's time." I got up and led him to the door but not right to it, still about 2 feet away. "You stand here, by the door, with your hands on it leaning. That way you can listen a little and if someone tries to come in you will be able to hold the door. Meanwhile I am going to blow you." I said with a smile as I got on my knees and squeezed between him and the door. It never occurred to me exactly what I was about to do, suck a cock. Never have I even thought about it but here I was about to willingly and wantingly do it.

I unzipped his jeans and reached in, surprised to feel silk. I whispered up and smiled, "You wearing panties?" He just nodded. I was just going to unzip and take it out but instead I pulled his pants down to his knees just to see and sure enough he had on blue silk tanga style panties on. I just drooled for a moment and then pulled his cock out. For the first time I had a cock in my face and I liked it. I licked it up and down, holding onto his legs. He moaned slightly so I kept that up for a bit. He wasn't large, maybe 6 inches at best, but a decent thickness. After letting my tongue run all over it I put it in my mouth inch by inch until I couldn't go any further and he was loving it by the sounds he was making. After I was used to it, I began moving up and down on it, shifting my hands from his legs around to his ass. I bobbed on his cock like I have had done to me and it was well appreciated. He was breathing heavy and began pumping into my mouth faster that I could move. I sucked and sucked, using my tongue as well, until I felt him tense up. Surprised enough not to move right away he shot into my throat all that he had. I gagged and swallowed as much as I could but some of it came out as I pulled off and got some onto my face. He relaxed against the door for a minute or two as I pulled his pants back up and got off the floor. When he saw the mess on my face he felt bad and came close and started to lick it off. I was so much more turned on now that when he was done I kissed him right on the lips hard using tongue and all. We stayed like that for a few moments then decided it was time to get cleaned up.

Meekly he said, "Thank you, that was so wonderful."

"My pleasure sweetie, I really enjoyed it. But I would change your underwear before going downstairs just to be sure no one sees them."

He agreed and soon we went to eat dinner. No one said anything unusual and so we got away with it. That was the first time, now the second.

The second time was ten days after the incident above. I had done some shopping for Brooke getting her some nice things, not too much though. A couple crop tops, two sexy bra and panty sets (one burgundy and the other navy crushed velvet), a pair of fake leather pants and pair of hip hugger jeans. All of which were nice trendy wear and I liked seeing them on girls so they should be perfect for Brooke. I loved shopping for her, as well as Beth. I feel it is nice to get the women in my life nice things. One Thursday I got a call from Beth.

"Mark, hey would you mind all too much if I went with my friend Cindy until Sunday? She wants to go visit her parents, it is their anniversary, and she doesn't have a car, neither her or her family can afford a plane ticket on such short notice, and she is afraid to ride the bus."

"Nah, hon, that's fine. We didn't really have any big plans this weekend and think it is nice of you to offer to take her. Go on, have a good time. Give me a call when you get there."

"Thanks bunches, I will most definitely call you. We will probably leave tonight since it is about an eight hour drive and get there early tomorrow morning. I better pack up a few things, will talk to you soon. Love ya."

"Love you too, be careful."

And with that I had the weekend free. I hadn't seen much of my friends so I made some calls but was striking out. Most were already busy but I did manage to make plans to meet a couple guys at the club Saturday night. So I figured I would just lounge around tonight and tomorrow, go out Saturday, and see Beth on Sunday. Least that was what I thought I would do. That changed though. Early Friday morning, Beth calls and wakes me up. No biggie at all.

"Wha...what, who is it?" I said sleepily.

"It's me hon, Beth."

"Oh, Ohhh, hi sweetie, how was the trip." I said through a yawn.

"I know I must have woken you, I'm sorry."

"Please don't be, I am thrilled to hear from you."

She gave a slight giggle, "Anyway, the trip went fine, not a problem. We are at her parents now and they were very happy to see her. We will be leaving here Sunday about noon and should get home in the evening. Can I just come over when we get in?"

"By all means, I will be here. Come on over."

"Great, I will see you then. Oh, by the way, can you do me a favor? Can you stop at my place and pick up the videos I rented and take them back? I would have my parents do it but they can be a pain about it. They always say 'I rented them, I return them. It is my responsibility.' So could you do that for me? They won't care if you do it, they consider us one person anyway." She said the last part with a laugh.

"Sure hon, I got it. Consider it taken care of."

"Cool. Well I'll see you in a few days, miss me. Love you."

"I will and I love you too."

And that was that. I soon went back to sleep but woke up not long after as my alarm went off. I got up, showered, dressed, went to classes for the morning. Afterwards, around oneish, I dropped by her place to get the movies. After a few knocks and ringing the doorbell, finally Eric came and answered the door. He looked at me like he wasn't expecting me.

"Hey there, I just stopped my to get the movies your sister rented to take them back. Can I get them?"

"Sure come on in, you know where her room is. Go on ahead and grab them."

"Cool, thanks." I walked up to her room and picked up the tapes and came back downstairs. "Hey, your parents home?" I asked with a wink.

He smiled a little and said, "Not right now, dad is working and mom is out with a friend shopping for a wedding gift."

"Well I would love to stay and fool around a bit but I have to get running. Got to take these flicks back and need to finish up some work for school so I can have a free weekend. Heyyy, I have a free weekend, you busy tonight Brooke?"

"Uhhh, I don't have anything planned really. Watch some tv, screw around on the computer."

"Great, here's the deal. I am going to call about 7 and say I need some work on my computer and I think you could help. I don't think your folks would mind at all you coming over to help me. We can go from there, how's that sound?"

"Sure, that would probably work. I..."

Before he could say anything else I said, "Great well I have to scoot. Call you later." And I left.

I dropped off the movies and went back to my apartment after getting some well needed groceries. I spent the next few hours doing some class work, finishing it up about 6. I got the new stuff I bought Brooke out and a little after 7 I placed my call. All worked as I thought it would and he was on his way over. I was so excited. It wasn't long before I heard him knock at my door. I let him in and closed the door. As fate would have it I had come across a computer problem this afternoon and asked him to take a look at it, I couldn't figure it out. He went right to it as I grabbed a couple beers. Took him all of about 10 minutes to sort it out, barely giving me enough time to get the beers opened it seemed.

"Thanks, you're the best. Here, have a beer. Ever had one before?"

"No this is my first, thanks!"

We sat down and bullshitted for a bit while we drank our brews. Then I said, "Brooke, I have done some shopping for you hoping to get the chance to give them to you. They are laid out on my bed, would you go try them on? Especially the pants over the jeans but make sure they all fit."

Half excited, half uneasy he went into my room and was gone for several minutes finally coming back out as I was opening another beer. Stunning to say the least, gorgeous is more like it. Wearing the pleather pants and off white crop top, nicely showing off her tummy, she came into the kitchen. She went to say something but I set my beer down and swept her into my arms and before she could speak I planted a heavy kiss on her, which she eagerly returned.

When the kiss ended I looked her in the eyes and smiled. "You look ravishing Brooke. Totally breathtaking." That made her blush hard.

"Ya know, you could pass as a real girl. Add a little makeup and that would be really ensured. Hmmm, I think...yes I do, come with me."

I led her by the hand to the bathroom where, upon looking, I found some of Beth's makeup she leaves here in case she spends the night. Never having used it before, I didn't really know what to do.

"Brooke, you ever try using this stuff?"

"A few times yeah, wasn't really good at it."

"Can you try it again?"

"Sure, I like to practice." And she went to work. I excused myself and went to grab my beer taking two big swigs of it effectively killing it. I left her alone and in 20 minutes she came back out. She did a good job, not the best but she said she wasn't great at it. But there was no way I was complaining, I liked it.

"Damn, hon, you did great. You look so incredibly hot!!!"

Blushing, "Thanks Mark, but you're just saying that."

"Not a chance, you are damn sexy. Any guy would want you!"

I went to her and kissed her once more, loving the taste of the familiar lipstick that Beth wears.

"Let's go out." I said.

"WHAT?? How??? I can't go out like this???"

"Sure you can, no one would even know. I'm serious" And I was. Although anyone really close may be able to tell, I wasn't planning on letting that happen.

"But...no I can't. And besides, it wouldn't look good anyone seeing you with me, another girl so to speak."

She had a point but I was thinking. For some reason I had to take her out and was bound to find a way. Ok, I had it. I would go move my car around to the back. We could sneak through the hall of my building and out the back door giving a minimal risk of being caught. I explained it all to her and with a little more coaxing, and another beer, I got her to agree reluctantly. I was so excited. I did everything as said and we got out without being noticed. We got in the car and went out the least used exit of the complex and went for a drive.

We drove for about 30 minutes to a suburb on the other side of town, where we really never went and knew no one. During the drive I would occasionally reach over and rub her leg. I even got her to lift her crop top to show me with set of undies she was wearing. She had decided on the burgundy ones, a nice choice. Of course they both were, I liked them equally. Only real difference in styles is these are French cut bottoms, the others are a thong. It was late evening, well dark, as we got to the other side of town. Not wanting to expose her too much her first time out, the only thing we did was went to one of those car washes that is open all night, where you wash it yourself. She got out for that as I washed my car, not that it needed it but I thought she would like to at least get out a bit. She seemed to be having a good time. I flirted with her a little, gave her small kisses, stuff like that. We had a great time and then we went back to my place. From seeing her and playing around, I was pretty worked up. She looked so hot!

We snuck back in quietly and as soon as I locked my door I was all over her. I never kissed anyone like I was kissing her that moment and she was returning the passion right back. I caressed her body as we made our way to the couch and continued there. Now I did something on accident. I left my curtains open. I had them that way earlier to get some fresh air in and, although I closed the window, I forgot about the curtains. I live on the bottom (basement) level so the window is high up on the wall and you really have to be looking to see in. I didn't notice this until afterwards though so back to the present. By now, we were really going at it on the couch. I got her top off and stood her up, back facing me. I got up behind her and nibbled at her neck and kissed her ears as I played with her chest through the bra and under it. She was panting quite hard and reached back to squeeze my crotch getting a handful of my hardening cock.

I reached around and undid her pants, sliding them to the ground. Having to bend down to do that, on the way up I stopped at her butt and focused my attention there. Yes I love butts and I really love hers. I kissed it and licked it and even gave a couple small bites on it, with one hand reaching beneath her legs and rubbing her cock. She was going wild now. After a few moments I sat back down after taking my pants and underwear off. She turned to face me smiling, sank to her knees in a sexy way and came right up to my cock and in one move took it all the way in her mouth. I gasped! Oh my was that the best feeling, and on top of that seeing her do it nearly sent me over the edge. I stopped her for a few seconds to get my grip and let her go on. She began a slow rhythm at first, building it up gently as she bobbed up and down. It was the sexiest thing I have ever seen. Her going down on me, on all fours, her panty clad ass in the air behind her. I slowed her down to a stop. Carefully, and with her help, I got her legs up and we went into a 69. As she resumed her blowjob, I firmly grabbed her ass as I kissed her cock through her panties. I loved it so much. With a quick hand I pulled the panties aside letting her cock come out. As I sucked on her with enthusiasm, I slowly slipped first one, then two fingers in her ass. She moaned nicely when I did that. We managed to keep quiet, as I don't want my neighbors to hear.

We kept the 69 going for a good amount of time. Each stopping when the other was getting close but finally I had to nail her. We got up carefully. She thought we were going to the bedroom but I couldn't wait so I bent her over my coffee table right there in the living room. Lining up my cock with that magnificent ass, I kept the panties aside and gently pushed my way in. I had forgot just how tight she was. I was going to try to make it last a long time but my body wasn't having any of that, I knew I wouldn't hold out long. So I went all out, thrusting in and out of this teen goddess as hard as I could, bouncing her thighs off my table some as she held on with all she had. I know she wanted to cry out but she muffled it well and whined some as I pounded her ass. In only a few minutes I felt it rising and unloaded the best orgasm ever, even better than the first one, deep inside her then literally collapsed on her back. I whispered to her how great that was and what a wonderful girl she is as I kissed her neck. But this time I wouldn't walk away without finishing. I slid off her back, pulled her a little ways away from the table, slid underneath her and took her cock in my mouth as I caressed her legs. Like a demon I sucked her and I knew she was loving it because soon she was face fucking me basically as I kept sucking and it wasn't too long before she shot her cum in my throat. I swallowed more of it this time though. She slid down and layed next to me as we cuddled together gaining our strength back. That was when I noticed the open curtains and quickly closed them. Not that I would be objected to it but I didn't want to get busted with another girl, especially my girlfriends younger brother.

That's not the end of the story, just this chapter. Look for more to come in the near future.

Comments are welcome but if your intention is to flame me, just keep it to yourself.

Freethinker32@yahoo.com


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate